Essentially, Skype staff divide possible video picture problems into two categories -- the technical or the lighthearted PICNIC (problem in chair, not in computer) category. A technical issue most likely involves the webcam or the software that makes it work on your or your colleague's computer. If the issue is that you can't see a live picture of yourself, the problem is on your end. If you can't see your colleague, the problem is likely on her end.
Skype allows you to connect with other Skype users as well as to call landline and mobile phone numbers. However, only calls between Skype users enable video calls and the ability to see the other caller. So if you've connected with someone who's using a phone outside of the Skype platform, you won't see her picture. If you are connected with another Skype user in a video call, not seeing video is akin to when you try to take a photo with a cap over the lens -- total darkness. So ensure that your and the other person's webcam are free of obstructions.
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Sometimes the webcam itself is the culprit. It could be broken or already in use by another program, so close any other open programs that use the webcam. Your calling partner also might need to update her webcam's drivers if its manufacturer issued an update to fix a bug or make it work more efficiently. Skype offers a number of recommended webcams that are available to buy from the Skype Shop (link in Resources). These webcams are, according to Skype, are ones that work seamlessly with the Skype platform.
Your calling partner might need to upgrade to the latest version of Windows, whether that's Windows 8 or otherwise. If that's not an option for him currently, he might need to download Skype's special version of the platform that's geared especially to those who have older computers and versions of Windows. Skype updates have prevented some older computer platforms from making Skype video calls. He can download the special version of Skype directly from the Skype website (see Resources). Beyond that, he can access his camera settings in Windows to see if they've granted access to Skype.
Skype continuously encourages users to ensure they have the latest version of Skype downloaded to provide better functionality. So that's something you and your fellow callers should do. Furthermore, to see if Skype is syncing properly with a webcam, you can click the Bar icon within Skype -- the button that looks like a bar graph. Then click "Webcam." From there you or your fellow callers can test to ensure that your webcams are working properly with Skype. If you or they use multiple webcams, ensure that the one being used is the one currently selected.